Tetrabutylammonium Fluoride → HCID 22496024, compound

HRID 1816007Notes

Reaction equation

HRID 1816007 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:43][Si](C(C)(C)C)(C)C)([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)C#N)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[O:43])=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22496050HCID 22496050, compound

Product 1

HCID 22496024HCID 22496024, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of TBAF in THF (1.0 M, 2.2 mL, 2.2 mmole) was added dropwise to a solution of (±)-3-(4-benzyloxyphenyl)-2-(ter-butyldimethylsilyloxy)-2-(pyridin-3-yl)propionitrile (769 mg, 1.73 mmole) in dry THF (10 mL) at −15° C. After 30 min, the reaction was partitioned between EtOAc and H2O. The layers were separated and the organic layer was washed with H2O, dried (MgSO4), filtered through a plug of silica gel, and concentrated to afford impure title compound (492 mg, 94%) as a yellow solid: MS (ES) m/e 304 (M+H)+. This material was used without further purification.

Workup

  1. customthe reaction was partitioned between EtOAc and H2O
  2. customThe layers were separated
  3. washthe organic layer was washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through a plug of silica gel
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8590528ae1ec47899148221c54bfa954
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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